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Vincamine

$64

  • Brand : BIOFRON

  • Catalogue Number : BD-P0610

  • Specification : 98.0%(HPLC)

  • CAS number : 1617-90-9

  • Formula : C21H26N2O3

  • Molecular Weight : 354.44

  • PUBCHEM ID : 15376

  • Volume : 25mg

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Catalogue Number

BD-P0610

Analysis Method

HPLC,NMR,MS

Specification

98.0%(HPLC)

Storage

2-8°C

Molecular Weight

354.44

Appearance

White crystalline powder

Botanical Source

Alkaloid from Vinca minor, Vinca major, Vinca erecta, Vinca difformis and Tabernaemontana rigida (Apocynaceae)

Structure Type

Indoles

Category

Standards;Natural Pytochemical;API

SMILES

CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(C2)(C(=O)OC)O

Synonyms

Methyl (12S,13aS,13bS)-13a-ethyl-12-hydroxy-2,3,5,6,12,13,13a,13b-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate/vincamine/(12S,13aS,13bS)-13a-ethyl-12-hydroxy-2,3,5,6,12,13,13a,13b-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij]-1,5-naphtyridine-12-carboxylate de methyle/(3a,14b,16a)-14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic Acid Methyl Ester/Pervone/Vraap/Methyl-(12S,13aS,13bS)-13a-ethyl-12-hydroxy-2,3,5,6,12,13,13a,13b-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij]-1,5-naphthyridin-12-carboxylat/Angiopac/Perval/Equipur/Vinca/Minorin/methyl 14-hydroxy-14,15-dihydroeburnamenine-14-carboxylate/Monorin/Decincan/Methyl (3α,14β,16α)-14-hydroxy-14,15-dihydroeburnamenine-14-carboxylate/Novicet/Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3α,14β,16α)-

IUPAC Name

methyl (15S,17S,19S)-15-ethyl-17-hydroxy-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18)-tetraene-17-carboxylate

Applications

Vincamine is a peripheral vasodilator, that increases blood flow to the brain.

Density

1.4±0.1 g/cm3

Solubility

Chloroform

Flash Point

261.6±30.1 °C

Boiling Point

508.9±50.0 °C at 760 mmHg

Melting Point

232ºC (dec.)

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2939990000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:1617-90-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

28216895

Abstract

Objective: Vincamine is a plant alkaloid used clinically as a peripheral vasodilator that increases cerebral blood flow and oxygen and glucose utilization by neural tissue to combat the effect of aging. The main purpose of the present study is to investigate the influence of vincamine on amyloid-β 25-35 (Aβ25-35) induced cytotoxicity, to gain a better understanding of the neuroprotective effects of this clinically used anti-Alzheimer’s disease drug.
Materials and methods: Oxidative stress was assessed by measuring malondialdehyde, glutathione, and superoxide dismutase (SOD) levels. Cell viability was assessed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. Cell apoptosis detection was performed using an Annexin-V-FITC Apoptosis Detection Kit. The production of reactive oxygen species (ROS) was determined using an ROS Assay Kit. Western blot detection was carried out to detect the protein expression.
Results: Our studies showed that pretreatment with vincamine could reduce Aβ25-35 induced oxidative stress. Vincamine markedly inhibited cell apoptosis dose-dependently. More importantly, vincamine increased the phosphatidylinositol-3 kinase (PI3K)/Akt and Bcl-2 family protein ratios on preincubation with cells for 2 h.
Conclusion: Above observation led us to assume that one possible mechanism of vincamine protects Aβ25-35-induced cell death could be through upregulation of SOD and activation of the PI3K/Akt pathway.
Summary: Vincamine ameliorates amyloid-β 25-35 (Aβ25-35) peptides induced cytotoxicity in PC12 cellsVincamine reduces Aβ 25-35 peptides induced apoptosis of PC12 cellsVincamine activates the phosphatidylinositol-3 kinase/Akt pathwayVincamine up-regulates the superoxide dismutase. Abbreviation used: Aβ25-35: Amyloid-β 25-35; AD: Alzheimer’s disease; BCA: Bicinchoninic acid; GSH: glutathione; PBS: Phosphate buffered solution; SDS: Sodium dodecylsulphate; SOD: Superoxide dismutase.

Title

Vincamine Alleviates Amyloid-β 25-35 Peptides-induced Cytotoxicity in PC12 Cells

Author

Jianfeng Han 1 , Qiumin Qu 1 , Jin Qiao 1 , Jie Zhang 2

Publish date

Jan-Mar 2017

PMID

30496743

Abstract

Diabetes mellitus is the most common endocrine disorder characterized by hyperglycemia resulting from defects in insulin secretion or insulin action. The present study was designed to investigate the antidiabetic effects of vincamine, one of the monoterpenoid indole alkaloid, in streptozotocin-induced diabetic rat model. Diabetes was induced in rats by an intraperitoneal injection of streptozotocin (40 mg/kg bw). Vincamine 20 and 30 mg/kg.bw were administrated orally as a single dose per day to the diabetic rats for 30 days. The vehicle control group received 0.5% dimethyl sulfoxide for the same duration. After 30 days of treatment, fasting blood glucose, glycosylated haemoglobin, total cholesterol, triglyceride, low-density lipoprotein cholesterol and very low-density lipoprotein cholesterol levels were significantly increased, whereas, body weight, plasma insulin, high-density lipoprotein cholesterol, antioxidant enzymes and reduced glutathione were markedly decreased in diabetic rats. Treatment with vincamine significantly restored these parameters to the normal level. The protective effect of vincamine was compared with glibenclamide, a well-known hypoglycemic drug. Our results clearly suggest that vincamine exhibit hypoglycemic, hypolipidemic and antioxidant activity. The anti-diabetic effect of vincamine was comparable to the protective effect of glibenclamide, suggesting its potential as a natural anti-diabetic compound with therapeutic benefits.

Title

Antidiabetic, Antihyperlipidemic and Antioxidant Effect of Vincamine, in Streptozotocin-Induced Diabetic Rats

Author

H S Nandini 1 , Prakash Ramachandra Naik 2

Publish date

2019 Jan 15

PMID

27664729

Abstract

Vincamine, a monoterpenoid indole alkaloid which had been marketed as nootropic drugs for the treatment of cerebral insufficiencies, is widely found in plants of the Apocynaceae family. Nerium indicum is a plant belonging to the Apocynaceae family. So, the purpose of this research was designed to investigate the vincamine alkaloids producing endophytic fungi from Nerium indicum, Apocynaceae. 11 strains of endophytic fungi, isolated from the stems and roots of the plant, were grouped into 5 genera on the basis of morphological characteristics. All fungal isolates were fermented and their extracts were preliminary screened by Dragendorff’s reagent and thin layer chromatography (TLC). One isolated strain CH1, isolated from the stems of Nerium indicum, had the same Rf value (about 0.56) as authentic vincamine. The extracts of strain CH1 were further analyzed by high performance liquid chromatography (HPLC) and liquid chromatograph-mass spectrometry (LC-MS), and the results showed that the strain CH1 could produce vincamine and vincamine analogues. The acetylcholinesterase (AchE) inhibitory activity assays using Ellman’s method revealed that the metabolites of strain CH1 had significant AchE inhibitory activity with an IC50 value of 5.16μg/mL. The isolate CH1 was identified as Geomyces sp. based on morphological and molecular identification, and has been deposited in the China Center for Type Culture Collection (CCTCCM 2014676). This study first reported the natural compounds tabersonine and ethyl-vincamine from endophytic fungi CH1, Geomyces sp. In conclusion, the fungal endophytes from Nerium indicum can be used as alternative source for the production of vincamine and vincamine analogues.

KEYWORDS

Endophytic fungi; Geomyces sp.; Nerium indicum; Secondary metabolite; Vincamine indole alkaloids.

Title

Indentification of Vincamine Indole Alkaloids Producing Endophytic Fungi Isolated From Nerium Indicum, Apocynaceae

Author

Ren Na 1 , Liu Jiajia 2 , Yang Dongliang 1 , Peng Yingzi 3 , Hong Juan 3 , Liu Xiong 3 , Zhao Nana 3 , Zhou Jing 3 , Luo Yitian 3

Publish date

2016 Nov